Best questions to ask to know someone better?

Here are some thoughtful and deep questions to ask someone to get to know them better:

• If you could visit any place in the world, where would it be and why?
• What’s your favorite way to spend a day off?
• What was the last thing you read?
• What’s the funniest moment you’ve experienced?
• Who do you look up to, and why?
• What's a skill you're interested in learning?
• Do you have any pets?
• What’s your go-to karaoke song?
• What was your favorite age growing up?
• What goal are you working toward right now?

Instead of just jumping from question to question, let the other person's answer guide the conversation. Really listen to what they're telling you and prepare for follow-up questions that you could ask about what they're saying. It'll keep you so much more engaged in the conversation if you're thinking about ways to expand upon what they're saying and ask them to give you more details.

Think about what you already know about the person and what they've told you in past interactions, then ask questions about those things. Maybe they mentioned a new job or that they're building a new house, or even a medical issue. So, for example, if the last time you saw them they said that their daughter was about to start up in a soccer league, you can make a point to ask them something like, "How is Sarah liking soccer?"